Imidazole → 2-(1H-imidazol-1-yl)pyridine-4-carbonitrile
Reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1>CN1CCCC1=O>[N:10]1([C:2]2[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=2)[CH:14]=[CH:13][N:12]=[CH:11]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 2-chloro-4-cyanopyridine (4.0 g, 28.9 mmol), imidazole (7.9 g, 115 mmol) and N-methyl-2-pyrrolidinone (50 ml) was heated at 150° C. for 58 hours. The solvent was removed by distillation and the residue was partitioned between chloroform and water. The organic layer was separated and the aqueous layer was extracted with chloroform (2×100 ml). The organic layers were combined and the solvent was removed in vacuo. The residue was triturated with ether and a solid was collected by filtration. The solid residue was purified by column chromatography eluting with hexanes/acetone (1/1) to afford 1.2 g (24%) of 2-(1-imidazolyl)-4-cyanopyridine as a tan solid, m.p. 146°-147° C.
Workup
- customThe solvent was removed by distillation
- customthe residue was partitioned between chloroform and water
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with chloroform (2×100 ml)
- customthe solvent was removed in vacuo
- customThe residue was triturated with ether
- filtrationa solid was collected by filtration
- customThe solid residue was purified by column chromatography
- washeluting with hexanes/acetone (1/1)
Sources & evidence
- ORD record
- ord-6eea1f5c84ee439a9c3bb3ccf73a418b
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05541187
Reaction notes
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